Soak The Corn Husks: Bring a medium pot or a teakettle filled with water to a boil and add corn husks to a large bowl or baking dish. Cover the husks with hot water and top with a tea kettle or pan to help the husks stay submerged. Soak the husks for at least 30 minutes or until they bend easily without breaking. Tear one or two husks lengthwise to create 1/4-inch wide strips to use for tying the tamales.TIP: Husks can be soaked up to two days ahead. Remove them from the water once pliable and store refrigerated wrapped in damp kitchen towels in a resealable container until ready to use.
Make The Sweet Potato Tamale Dough: Bring 3 cups of water to a boil in a medium saucepan. Place the masa harina in a bowl then pour in the water and stir to combine. Set the masa aside to hydrate, about 15 minutes. Once the masa is hydrated, place the sweet potatoes, hydrated masa harina, coconut flakes, pecans, brown sugar, coconut oil, baking powder, vanilla extract, kosher salt, 1 1/2 teaspoons of cinnamon, and cloves in a stand mixer fit with a paddle attachment. Mix over medium until everything is well incorporated and airy, about 5 minutes, stopping the mixer and scraping the dough down the sides as needed.TIP: Tamale dough can be made up to two days ahead of time. Store refrigerated in an airtight container and bring to room temperature before proceeding.
Place 24 drained corn husks on work surface. Divide the masa among the husks, placing the mixture in the middle of each husk and, using your hands, shape it into a rectange about 1-inch thick. Fold long sides over filling, then tie ends of tamale shut with husk strips. Repeat process to make 24 tamales.
Cook The Tamales: Use a tamale steamer or a steamer insert, set inside a large stockpot and add water to just below bottom of the steamer insert (make sure the water doesn't touch bottom of the insert). Cover and bring water to boil. Arrange tamales in the pot upright, leaning against one another. Cover and steam until dough is slightly firm to touch and separates easily from husk, adding more water to pot as necessary. Arrange tamales in the pot upright, leaning against one another. Cover and steam until dough is firm to touch and separates easily from husk, adding more water to pot as necessary, about 40 minutes.
Make The Spicy Chocolate Sauce: Meanwhile, make the sauce. Slice off stem end of each chile and remove seeds. Heat a large frying pan over medium heat, then toast chiles, turning frequently, until fragrant and beginning to darken, about 30 seconds. Transfer to bowl, cover with boiling water, and soak 20 minutes. Meanwhile, place chocolate and coconut milk in top of a double-boiler and melt over medium heat, stirring until smooth. Remove from heat, drain chilies and combine in blender with 1/2 cup of orange juice, maple syrup, and remaining 1 teaspoon cinnamon. Blend until very smooth. Taste and adjust flavoring as desired. TIP: The chocolate sauce can be made up to two days ahead of time. Store refrigerated in an airtight container and bring to room temperature before proceeding.
Serve The Tamales: Once the tamales are cooked, remove them from the steamer and let cool until you can unwrap them. Serve unwrapped tamales garnished with chocolate sauce, a drizzle of coconut milk, and some cacao nibs.